Preparation of a New Spirobi[thieno[2,3- c ]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives

Vasudevan Dhayalan; Fernando Rabasa Alcañiz; Veronika Werner; Konstantin Karaghiosoff; Paul Knochel

doi:10.1055/s-0035-1560187

Preparation of a New Spirobi[thieno[2,3- c ]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives

Vasudevan Dhayalan, Fernando Rabasa Alcañiz, Veronika Werner, Konstantin Karaghiosoff, Paul Knochel

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

3-Thienylacetic acid was converted in six steps into a new spirobi[thieno[2,3-c]pyran] (overall yield: 52%). The spirobi[thieno[2,3-c]pyran] was selectively mono- or dimetalated with butyllithium and then transmetalated with zinc chloride; cross-coupling reaction with various aryl or heteroaryl bromides, including bromo-oligothiophenes, acid chlorides, and 1-bromopyrene, produced the corresponding spiro derivatives in high yields.

Original language	English
Article number	ss-2015-t0435-op
Pages (from-to)	3972-3982
Number of pages	11
Journal	Synthesis (Germany)
Volume	47
Issue number	24
DOIs	https://doi.org/10.1055/s-0035-1560187
State	Published - 17 Dec 2015
Externally published	Yes

Keywords

lithiation
Negishi cross coupling
oligothiophene
organozinc reagent
spiro compound

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0035-1560187

Cite this

Dhayalan, V., Alcañiz, F. R., Werner, V., Karaghiosoff, K., & Knochel, P. (2015). Preparation of a New Spirobi[thieno[2,3- c ]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives. Synthesis (Germany), 47(24), 3972-3982. Article ss-2015-t0435-op. https://doi.org/10.1055/s-0035-1560187

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abstract = "3-Thienylacetic acid was converted in six steps into a new spirobi[thieno[2,3-c]pyran] (overall yield: 52%). The spirobi[thieno[2,3-c]pyran] was selectively mono- or dimetalated with butyllithium and then transmetalated with zinc chloride; cross-coupling reaction with various aryl or heteroaryl bromides, including bromo-oligothiophenes, acid chlorides, and 1-bromopyrene, produced the corresponding spiro derivatives in high yields.",

keywords = "lithiation, Negishi cross coupling, oligothiophene, organozinc reagent, spiro compound",

author = "Vasudevan Dhayalan and Alca{\~n}iz, {Fernando Rabasa} and Veronika Werner and Konstantin Karaghiosoff and Paul Knochel",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart New York Synthesis 2015.",

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Dhayalan, V, Alcañiz, FR, Werner, V, Karaghiosoff, K & Knochel, P 2015, 'Preparation of a New Spirobi[thieno[2,3- c ]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives', Synthesis (Germany), vol. 47, no. 24, ss-2015-t0435-op, pp. 3972-3982. https://doi.org/10.1055/s-0035-1560187

Preparation of a New Spirobi[thieno[2,3- c ]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives. / Dhayalan, Vasudevan; Alcañiz, Fernando Rabasa; Werner, Veronika et al.
In: Synthesis (Germany), Vol. 47, No. 24, ss-2015-t0435-op, 17.12.2015, p. 3972-3982.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Preparation of a New Spirobi[thieno[2,3- c ]pyran] and Its Selective Mono- and Dimetalation

T2 - Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives

AU - Dhayalan, Vasudevan

AU - Alcañiz, Fernando Rabasa

AU - Werner, Veronika

AU - Karaghiosoff, Konstantin

AU - Knochel, Paul

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York Synthesis 2015.

PY - 2015/12/17

Y1 - 2015/12/17

N2 - 3-Thienylacetic acid was converted in six steps into a new spirobi[thieno[2,3-c]pyran] (overall yield: 52%). The spirobi[thieno[2,3-c]pyran] was selectively mono- or dimetalated with butyllithium and then transmetalated with zinc chloride; cross-coupling reaction with various aryl or heteroaryl bromides, including bromo-oligothiophenes, acid chlorides, and 1-bromopyrene, produced the corresponding spiro derivatives in high yields.

AB - 3-Thienylacetic acid was converted in six steps into a new spirobi[thieno[2,3-c]pyran] (overall yield: 52%). The spirobi[thieno[2,3-c]pyran] was selectively mono- or dimetalated with butyllithium and then transmetalated with zinc chloride; cross-coupling reaction with various aryl or heteroaryl bromides, including bromo-oligothiophenes, acid chlorides, and 1-bromopyrene, produced the corresponding spiro derivatives in high yields.

KW - lithiation

KW - Negishi cross coupling

KW - oligothiophene

KW - organozinc reagent

KW - spiro compound

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Preparation of a New Spirobi[thieno[2,3- c ]pyran] and Its Selective Mono- and Dimetalation: Application for the Preparation of Soluble Conjugated Oligothiophenes and Pyrene Derivatives

Abstract

Keywords

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